The Best of Times
by Scarlett Rogue
Summary: Fem!Cas, Fem!Sam. Pure smut. Sam, Dean and Cas take a break from hunting to enjoy each other for the night. Destiel, Wincest, Wincestiel.


Dean's head was swimming with lust, eyes blown wide as Cas brushed her chapped lips along his inner thigh, too close to his growing erection but not close enough. Meanwhile, Sam had her legs wrapped around Dean's waist, fingers carded through his hair and teeth biting into the skin of his neck. A groan filled the room as Dean pushed his hips forward. Cas smiled up at him and got on her knees, brought her face over Dean's shoulder to press her lips to Sam's. Dean squirmed as the two women moaned into each other's mouths; all he wanted was to feel lips wrapped around his cock, wet mouth sucking him in. Instead he got Cas rubbing her small palms over his legs, skipping his clothed member each time.

Sam ran one hand down Cas' arched back, over her firm ass and gave it a squeaze, followed by a harsh slap that had Cas moaning sharply and falling forward against Dean, her naked cunt pressed against his underwear, and Dean wanted to pull away from Sam, push Cas down on the bed, spread her legs and fuck into her fast and hard, but Sam's legs were unbearably strong and held Dean in place. To his satisfation, Sam used her other hand to push the fabric of Dean's underwear down enough to grip his cock and pull it out. Dean shivered as the head rubbed against Cas' wet lips while Sam began stroking him at the same time.

"Cas, fuck, come here," Dean growled before pulling Cas against him and smashing their lips together, finesse be damned. He pushed his tongue passed her lips, into the heat of her mouth, letting his other hand trail up to play with her small breasts. Cas jerked forward as Dean pinched her nipple and accidentally rubbed her soaking core against the head of his cock again.

"Okay, fuck foreplay!" Dean pushed Cas away lightly, gripped Sam's legs, and pulled them away so unexpectedly that Sam didn't have time to stop him. Dean was momentarily upset about the loss of Sammy's hand around his length, but he got over it quickly when he spun around on the bed and got a good look at his little sister.

Dean didn't think he'd ever appreciated how beautiful Sammy truly was, and for good reason. They were family, for fuck's sake. He never wanted to see Sam like that. It was impossible, however, to ignore her beauty any longer the day he walked in on Sam completely naked, spread out across the shitty motel bed, back arched and hands wrapped in Cas' hair as the angel made her come with just her tongue.

That was the first day they had a threesome, when Sam looked over at Dean, smiled with those puppy dog eyes and beckoned for him to come closer so she could suck him off while he fingered Cas to orgasm. They never looked back after that.

Seeing Sammy now, legs spread, tight cunt dripping wet on the sheets, was like the first time all over again.

"You just gonna stare, huh Dean?" Sam smirked, ran her fingers between her legs, and brought them up to Dean's mouth. He took them in instantly, licking the sweet juices that he had become so familiar with.

"On your back, Dean." Sam's fingers slipped out of his mouth as Cas pulled him back onto the bed.

"I was busy there!"

"You promised it was my turn to be in control, so you'll be a good boy, won't you?" Cas asked, no, _demanded_, and fuck if that didn't make Dean's cock swell to an impossible extent. Dean nodded, watched as Cas moved down the bed to Sam, who spread her legs and locked her eyes with Dean's.

A few seconds later Sam moaned loud, jaw dropped, and Dean looked down to see three fingers buried in her tight hole, moving in slow, deep thrusts. Sam and Cas had been messing around long before they included Dean, and Cas knew just how to twist her fingers to made Sam's head fall back in a near howl of pleasure. Cas took Sam's nipple between her lips, nibbling gently, as she pushed a fourth finger into Sam's body, and bless her, she took everything Cas gave her and moaned like a little slut.

Dean hadn't even realized that he was arching his hips off the bed, practically fucking the air, until Cas placed a hand on his leg and held him to the mattress with angelic strength, and Dean decided in that moment that Cas needed to be in control more often. As much of a tease as it was, Dean had no doubts that he would enjoy this night more than most.

"Fuck, Cas, ugh, more, I need more-" Sam mumbled as she raked her nails along Cas' back.

"Do you want Dean's cock now?" Cas asked. The soft, sweet tone Cas was using drove Dean crazy; it was too controlled, and Dean knew that Cas was holding back her own lust. He couldn't wait for her to unleash it all, whether it was on him or Sam, or both.

"Ye-AH! Yes, fuck, I need Dean's cock in me right now, need to be fucked hard, Cas..."

Cas pulled her fingers out quickly, too fast perhaps, but Sam loved the feeling of Cas' nails dragging over her soaking pussy too much to complain, only whining when she was left empty and unsatisfied.

"I want you to climb on top of Dean and ride his cock." She didn't have to say it twice. Sam climbed shakily on Dean's lap, grabbed his cock, lined herself up with him, and sunk down in one quick motion. Dean cursed as heat wrapped around his length, sucked him in deep until he hit the back of Sammy's cunt and his sister panting on top of him. She stayed that way for several seconds, until Dean was shifting his hips and trying to fuck up into her, Cas' hand on his leg stopping him.

"Damnit, Sammy, fuck me! Know you want to come on my cock."

Sam's pupils dilated noticeably and she placed one palm on his abdomen, the other kneading her tits, and began bouncing on his lap, drawing his cock out of her and back in quickly.

Dean didn't have time to enjoy the view before he felt Cas' hand pull off his leg and watched her climb over him, position herself so that both legs were on either side of Dean's head and her pussy was in his face. She didn't have to say anything, just grabbed his hair and pulled his head up the few centimeters it took for him to wrap his lips around her clit and suck.

It quickly became a competition of who could hold off their orgasm longer. Sammy would lose, Dean was sure, what with all the build up she had gotten and the thick cock pounding into her g-spot. Dean knew she was close when she stopped bouncing, just sat on his cock and rutted her hips forward and back quickly.

Cas would last the longest as always. Even now, with her wrecked moans filling the room, still relatively new to the feeling of having a warm tongue fuck her hole, she would last the longest. She held on to Dean's hair and rode his face, shivering every time he groaned into her skin and felt it vibrate through her clit.

"I'm gonna- ah, fuck, Dean! Your cock feels so good, I'm gonna-"

Dean groaned as Sam clenched around him and a new wave of slick heat washed over his member. Sam's screams filled the room and she fell forward as she came, in her lust-blown state biting down on Cas' neck and reaching around to stroke her clit furiously. Dean smirked, lips coated in cum, and began fucking Cas' pussy fast and hard with his tongue, angling as much as he could to reach her g-spot. It was difficult to say the least, and his tongue was sore after only a few seconds of the hard position, but it was worth it to watch Cas' eyes roll back into her head as she came over his mouth, the feel of Dean's tongue inside her and Sammy on her clit too much to hang on.

Dean pulled his tongue out of Cas and licked her clean, the taste of her driving him mad, and he was so close now, just needed the tiniest push to spill his load. Sam climbed off his lap slowly then got to her knees, running her tongue over his length. A few seconds later Cas joined her. It was all Dean would do to grip the sheets and watch the two women, his sister and his best friend, suck him off at the same time, their tongues rubbing together at times. Sammy dragged the head of his cock into her mouth but didn't move, sat there as Cas licked up and down the length of his cock, and Dean came without warning, spilling his load in Sammy's mouth and watching through sweat-slicked lashes as she swallowed every last drop.

Sam and Cas kissed momentarily, swapping spit and Dean's come, and then they were next to him, laying across his chest and pressing kisses to his warm skin.

Through all the thoughts flying through his mind, anywhere from what an amazing orgasm that was to how damn lucky he was to have two women who loved him and loved each other, who wanted to share these experiences as a group, only one thought begged to be voiced.

"You came before me," he teased. Cas nipped at his ear playfully.

"Shut up," she said with a tiny twitch of her lips. Sam chuckled, low and tired, against Dean's shoulder. Sam and Dean sunk quickly in to sleep, and Cas watched her hunters, memorizing every tiny aspect of their post-sex happiness, never wanting to forget the best times they had ever had.

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